White Sox: Three biggest missed opportunities

The Chicago White Sox had a very productive offseason and there’s no question about that. But, could it have been better than it ended up being? 

Personally, I believe the answer is yes. I will also acknowledge, though, that the same could be said about pretty much every franchise.

There’s not a team in baseball that absolutely accomplished everything they should have this offseason, except for maybe the New York Yankees whose only goal was to make sure Gerrit Cole was wearing pinstripes in 2020.

Even they, though, missed out on some opportunities to improve their roster further despite achieving their goal.

The White Sox are no exception to this rule and I think that there are certainly some areas that could have been improved better.

One position that could not have been improved was the catcher spot where Yasmani Grandal was without question the perfect acquisition for the team as exemplified by his number one ranking among catchers in the game right now by MLB Network.

There’s a lot to be excited about on the South Side in 2020, but it could have even been better if any of these three potential signings came to fruition.

1. Zack Wheeler

The Chicago White Sox appeared to make the right-hander their top target from the get-go when it came to signing starting rotation help.

At one point, it appeared that the White Sox were the frontrunners for him and it was later revealed that they made the highest bid to sign him.

However, he chose to sign a five-year, $118 million contract with the Philadelphia Phillies instead which left the White Sox scrambling to their fallback options.

Had the team signed Wheeler, he probably would’ve slotted in right behind Lucas Giolito in the rotation. That’s a spot in the rotation that Dallas Keuchel, at least as of right now, will call his home in 2020.

Wheeler, 29, was coming off a season with the Mets in which he had a 3.96 ERA, 3.48 FIP, 8.98 K/9, and 2.30 BB/9. His walk rate and fWAR (4.7) were the best of his career so far.

Long term, Wheeler seems like a good bet to continue improving and the fact that he threw 195 1/3 innings in 2019 suggests that his health issues of the past are behind him now.

Having an arm with the potential to breakout like Wheeler would have been really nice behind Giolito.

2. Stephen Strasburg

The White Sox actually might’ve pivoted to this right-hander after Wheeler signed with the Phillies as Jon Morosi of MLB.com reported that they were a “dark horse” to sign Strasburg.

Whether or not they actually did make an offer for him is unknown, but it certainly was a missed opportunity.

In fact, it could be argued that it was a bigger one than Wheeler as Strasburg is an established ace coming off a year in which he won World Series MVP for the Nationals.

The 31-year-old registered a 3.32 ERA, 3.25 FIP, 10.81 K/9, and 2.41 BB/9 in 2019. He also had a 5.7 fWAR, which was the second-highest mark of his career and his 209 innings of work were the highest he had thrown since 2014 (215 innings).

Strasburg’s age coupled with the seven-year, $245 million contract it took the Nationals to keep him might have made the White Sox balk at signing him.

Had the White Sox signed him, though, the team would have had instant credibility with a one-two punch at the top of the rotation that would’ve been second to none.

Their reluctance to sign Strasburg is very understandable, but it would have put made a statement to the American League if they got him.